This is an end of an era film for Woody Allen in a way. The last time he really experimented with form, doing a musical. (He used to try to mix up the form every few movies - meta rom com, sci fi, Fellini-esque, pseudo documentary - but after this basically stopped taking visual risks). It's a lively piece with some fun numbers and tunes.
It was also the first time he had some spectacularly awful casting - Julia Roberts and Woody are an utterly mismatched pair. I love Julia Roberts, her acting is lovely but she's totally not suited to being with Woody; it started a depressingly long trend where he was teamed with much younger actors and where that age difference wasn't the point of the story. The flipside of that is that this has some really nice casting - Drew Barrymore's role was something of a turning point for her, she'd normally played vixens as a grown up but the "good girl" type she plays here would be a lot more lucrative for her; Natasha Lyonne had her first lead role with this; it's early parts too for Natalie Portman, Billy Crudup and Edward Norton. Goldie Hawn plays the Mia Farrow role. Tim Roth is hilarious as an ex con.
The musical conceit has the actual actors singing - like what Peter Bogdanovich tried to do with At Long Last Love. Like that this is a shaggy dog story among the rich - Allen's feels like it should have been set in the 30s, with its (mostly) super rich protagonists living a la la lifestyle, but was set in the present in day, presumably for cost.
It ambles along. There's some funny jokes. The last half hour is a drag because the key subplots have resolved (Barrymore is back with Norton, Roberts has dumped Allen) and the climactic number is between Allen and Hawn (who we've hardly spent time with). It was having a good time until then.
Some scenes make me a little awkward, I admit, considering the allegations against Allen: Natalie Portman running around on the beach in a swimsuit when she was very young; super young Lyonne being sexually precocious at 17 (I think - though is she meant to be older than Drew Barrymore?) and telling her father she wants to get marriage.
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